Perfume



Patented Aug. '15, 1939 UNITED STATES PERFUME Albert Weissenborn, Dessau-in-Anhalt, Germany, assignor to Winthrop Chemical Company, Inc., New York, N. Y., a corporation of New York No Drawing.

Application June 1, 1938, Serial No. 211,204. In Germany June 15, 1937 4 Claims.

In Recueil des Travaux Chimiques des Pays- Bas, 1935, pages 995 et seq., ketals'are described which are produced by condensing pyrocatechol with aliphatic ketones. Ketals have not hitherto 5 been used for making perfumes; thus on page 998 of the above application the condensation prodnot from acetone and pyrocatechol is stated to have a peculiar odor, but, owing to the resemblance of the latter to that of aromatic hydrocarl bons and also on account of the comparatively low boiling point of the ketal, the product is not suitable for use in perfumery.

This invention relates to the application in perfumery of ketals of the aforesaid kind which 15 contain in the ketone residue at least 6 carbon,

atoms but at most 9 carbon atoms, for these bodies possess perfumes which difier widely from those of the ketals of lower molecular weight and, therefore, are very useful in compounding 20 new perfumery mixture. Ketals having more than 9 carbon atoms in the ketone residue are useless, since they are substantially without odor. The ketals in question are derived, therefore, from pyrccatechol and dipropyl ketone or diisopropyl ketone or the corresponding butyl ketones (symmetrical ketones) or even unsymmetrical ketones, for instance methyl-butyl ketone or methylamyl ketone. The character of the odor of ketals from symmetrical ketones resembles that of'natural geranium oil or of the rose. Especially suitable is the diisopropyl pyrocatechol ketal ofthe formula 50 teristic of jasmone and amyl cinnamic aldehyde which. are the best jasmin compounds. This compound corresponds with the formula and when pure resemblw water in appearance m I and boils at 100 to 102 C. under mms. pressure.

The following examples illustrate the invention:

- EXAMPLE 1 Artificial geranium oil 5 Per cent Diisopropylpyrocatechol ketal 25 Phenylethyl alcohol 15 Geraniol, 41 Diphenyl ether 4 10 Citronellol R 100 EXAMPLE 2 p 15 Rose Per cent Citronellol R 22 Geraniol 25 Phenyl ethyl alcohol 2o -Nerol 5 Methylinnnnn 4 Fhenylacetlc acid (10% strength) 4 Phenylacetaldehyde (10% strength) 2 Diisopropylpyroeatechol ketal 6 Nonyl aldehyde (10% strength) 2 95 100 Exmm 8 Jasmin 30 Per cent Methylamylpyrocatechol ketal 6' 'a-amylcinnamic aldehyde 20 IBenzyl acetate 30 Linalool 10 Benzyl salicyla 10 Cinnamic alcohol 3 Hydroxycitronellal 6 Linalyl acetate 3 40 Indol (10% strength) -1-.." 5 Phenylethyl alcohol 2 p-acetonaphthone 5 100 EXAMPLE 4 Jasmin Per cent Methylamylpyrocatecholketal 5 a-amylc'innamic aldehyde 10 Benzylsalicylate 10 Hydroxycitrn 10 Phenylethyl alcohol 10 Benzylbutyrate 2.5

Linalyl aceta 5 Terpineol 7.5 Benzyl acetate 40 atoms 2. Perfumes containing as a constituent methylamylpyrocatechoi ketai of the formula 3. Perfumes containing as a constituent diisopropylpyrocatechol ketal or the formula 4. Perfumes containing as a constituent a butylpyrocatechol ketal of the formula ALBERT WEISSENBORN. 5 

